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4 Days in Down-East Portland

Last Updated on August 3, 2023

Portland Head Lighthouse, Maine
Portland Head Light is the most photographed lighthouse in the country (although I’m unsure who’s keeping the official tally).

Portland, Maine, is the latest stop on my genealogical journey, which so far has brought me to Germany, Lithuania, Florida, and a few places local to my hometown of New York, where I’ve met countless newfound aunts and cousins of various degrees and steps-removed. This time, a new-found Pittsburgh cousin and his pup (a duo I refer to as Mutt and Jeff) came along for the ride to visit his niece, who recently relocated Down East from Chapel Hill.

Jeff and I managed to meet up with Michele twice during our three full days here. In between, we’ve explored the town by boat, car, and foot, spending a notable amount of time in Portland’s Old Port neighborhood, which still has cobblestone streets and historic buildings dating back to the 19th century (just after the fire of 1866, which destroyed much of the city).

With a population of just over 68,000 inhabitants, Portland is on the sleepier side, which is part of its charm. But for a city of that size, it boasts a surprising amount of independent bookstores and top-notch dining (Bon Appetit named it Restaurant City of the Year in 2018). So we were more than satiated over the course of our stay. Here are the highlights.

Wadsworth-Longfellow House

Interior of the Wadsworth Longfellow House in Portland, Maine
Inside the former dining room of the Longfellow House, where Henry Wadsworth Longfellow spent his childhood.

Even though the eminent poet lived in the house only until his early teens, he returned often for visits and is thought to have penned some of his poems here. The home brims with artifacts from his family, providing a glimpse into domestic life in the 19th century. Guided tours are under an hour and the house is smack dab in the middle of town, making it easy to squeeze in a visit. Purchasing tickets ahead of time is recommended as the size of tour groups is limited. Entry to the backyard garden is free.

City Van Tour

Although we could have easily driven around town on our own, we opted for a van tour so that we could have a local show us around and learn some history. And Derek of The Real Portland Tour didn’t disappoint. Not only did we visit three lighthouses and drive past all the main landmarks, but we got an earful of local lore and even a sample of Derek’s slam poem about the little-known facts of his hometown — all delivered in a Down East drawl with plenty of humor. I recommend taking this tour on one of your first days there so you can map out which spots you want to revisit and also to hit up Derek for suggestions on where to eat. Points visited on the tour included: Bug Light, Fort Williams Park and Portland Head Lighthouse, Munjoy Hill, Portland Arts District, and several more.

Schooner Cruise

Jeff and Max on Peaks Island, Maine
Mutt (Max) and (cousin) Jeff in the back of my friend’s pickup on Peaks Island

Considering Maine’s coastline is longer than California’s, a day on the water is a natural way to get a taste of local flavor. You can take your pick of maritime transportation options, including kayaking in Casco Bay, taking a ferry to one of the outlying islands, or even jumping on the mailboat to island hop. An old salt, Jeff chose to kick back on the deck of a schooner, which took us through the bay and gave us a different view of the many lighthouses we’d seen on the van tour, as well as closer-up views of Fort Gorges and the privately owned (and heavily guarded) Cushing Island. Note that tickets are far cheaper if purchased through the Portland Schooner Co. website than those of third parties — TripAdvisor’s price was nearly double.


With five times the average number of bookstores for a city its size, Portland is a bibliophile’s haven. In addition to its five indie bookstores, the Forest City also boasts a number of rare and used shops.  Almost every Portlander we asked directed us to Longfellow Books, one of the oldest in town and located a few blocks away from its namesake’s childhood home. On my next trip, I plan to hit up one of the locations for Sherman’s Maine Coast Book Shops and second-hand specialist Yes Books.

Vegan Eats

Shops in Old Port Portland, Maine
Old Port’s streets are lined with curiosities, art stores, and delicacies, all packaged in 19th-century architecture.

A seriously foodie city such as Portland knows how to cater to a wide range of diets and appetites, so finding good vegan grub wasn’t difficult. In fact, most every menu we saw had at least one animal-friendly option (although some were more creative and accommodating than others). The rad nar at Ruby Thailand was deliciously thick with yellow-bean gravy, while the mushroom-based poutine at Copper Branch (a Quebec-based chain) tasted like the real thing (as much as my taste buds could remember from more than 20 years ago).

I’d like to visit Maine in the spring to sample some in-season fiddleheads, which I hear are a state delicacy. Derek also regaled us with his tale of the rivalry between his home state and Pennsylvania, both of who claim to be the origin of the whoopie pie, Maine’s official state treat. (Blueberry pie is the official state dessert.) I may try to veganize a recipe for needhams, as I’m fascinated by the idea of combining chocolate, potatoes, and coconut.


Jeff, Max and I stayed at a cute Airbnb in South Portland that was incredibly affordable considering how spacious it was — less than $300/night for a two-bedroom apartment in a 1900 multi-unit home. Our tour guide also told us about the Spring Point Inn, run by the hospitality department of Southern Maine Community College, which is right on the water and has stunning ocean views from many of its rooms.


  1. Portland,Maine is not down east Portland!! Downeast Maine is Stonington, Deere Isle etc… Portland is Southern Maine! I’m a born and raised Mainer! If you dont know where you are or what to call it. Ask a lical!!

    • I’m sorry if I made a mistake with the terminology. I was using the term as one of my tour guides did. However, he’s a local, not a lical like you are, so perhaps that’s the reason for the different usage.

  2. I’m glad you had fun. Mainers would be very upset with the suggestion that Portland is down-east. It is very much not located down-east. While it might feel fun to use a local phrase it isn’t merely a saying. The people here actually use it as reference to an area of the state.

    • I appreciate your comment. To give you some background, before I used the term (to disambiguate it from its larger namesake in Oregon), I researched the definition and found several reputable sources to support the way I used it on the blog. In doing so, I learned that the term can have a variety of meanings, depending on where you are. While Mainers use it one way (and, it seems, even that can vary by region), the use outside of Maine is in reference to the state as a whole. A few places that support my use include AP Style Guide, Jeopardy! (where its use of the term sparked a huge debate), and the state magazine of the same name.

      I do, however, understand that this is a touchy subject for Mainers. I imagine it is much like the disagreement around the term “upstate” in New York. I’d be happy to hear any suggestions you might have as to how the title could be changed to be accurate to more readers.

  3. Jeffrey Meyer

    My favorite bumper sticker – “Portland sucks. Tell all your friends”.

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